Birthday Escape to Kennebunkport, Maine
This year I wanted to celebrate my life in epic proportions. I started by checking out The View from the Prudential Center in Boston which was amazing and I would highly recommend. This was followed by appetizers at Long Bar located at the Raffles.
I still really wanted to get away to celebrate 34 years on earth! I’d previously booked a one-night stay in Newport, Rhode Island, in celebration of my birthday and found that to be very memorable.
In a similar train of thought, I decided to book a one-night stay in Kennebunkport, Maine to celebrate my 34th birthday. I had actually seen pictures of an adventure my sister embarked on to the city and thought it had potential to be delightful in the winter. This destination was noted in Apple Maps to be about a one-and-a-half-hour drive from Boston, where I reside.
I hopped on the internet and found accommodation at The Colony Hotel that looked quite renovated and beautiful with views of nature, rivers and even the Atlantic Ocean.
My boyfriend and I each packed our one-night carry-on in the morning and left around 11 AM; arriving by car around 1 PM. While I typically create extremely detailed itineraries, I decided I would chat with GPT for ‘things to do in Kennebunkport, Maine’ on the ride up and we would truly wing this trip!
We were delighted because there had been a recent snowfall that left every tree frosted with snow, making the views from the Ford Bronco on the drive up truly magical.

We arrived at The Colony Hotel, and it was actually a ginormous gilded-age mansion that, in the winter, is uninhabited because the old building doesn’t have a heating system.

There was a brand-new addition across the way with views of a river that leads into the Atlantic Ocean. We drove to the Coveside Market, where we checked in with the Barista/Hotel Manager. He was super nice and gave us our keys to the room. We dropped our bags in the brand-new building that has only been in service for about a year or two. I loved the blue and pink paint in the hallways and hydrangea print chair. The duvet was the warmest and actually the nicest duvet I’ve ever encountered. I hope to get one of my own in the future.

After dropping off our bags, we drove to see the Bush compound from Walker’s Point about a 2-minute drive from the accommodations.


We then ventured into the town area where we parked for free and then checked out all the little boutiques and shops that were open in the Winter. We loved the decorative hearts that were all around the town.





I had looked into staying at the Kennebunkport Inn and wanted to check out their winter dining experience. We decided on the spot to get lunch/dinner around 4 PM without a reservation at The Burleigh. While the outdoor red gondola experience was booked up for the entirety of February, we decided to snag a table near the bar. I had the haddock with carrots and mashed potatoes, and my boyfriend had the chicken and risotto dish. We were so happy with our choices.


Afterward, we picked up our car from the parking lot and admired twilight on the water.

We drove back to see the sunset along the Atlantic Ocean along Ocean Avenue, which is the road you take to get to the Bushes’ compound. This is a must because the views are truly gorgeous, even if the actual sun is not in plain sight.


We then drove back to the hotel and chilled out in our suite!
What we would come to find out is that the hotel may need to work its marketing efforts because we were the only car in the entire lot and had The Colony Hotel entirely to ourselves. This was semi-scary to me in many ways but then also a weirdly unique and magical experience. It was like I was on my own compound, hah!
We watched television together, something we honestly rarely do!
The next morning, we got up slowly. They had really nice Nespresso pods in the hotel room, so the coffee was immaculate. We got dressed, and I did my makeup in the brightly lit bathroom. I stood on the porch for one last time and then ran down the long pink hallway because the entire building was empty! We checked out by 11 AM. Here are pictures outside the new building and the older building, views from the summer salt water lap pool that overlooks the Atlantic ocean and views down the pink hallway.



They kindly gave us a voucher for breakfast sandwiches in the morning at The Coveside Market, which was delightful. I sipped a coffee and snagged a cute postcard before we were on our way.
We hopped into the car and then ventured to Gooch’s Beach. This was beautiful, paired with Taylor Swift and Lana Del Rey’s song “Snow on the Beach.” You can see The Old Colony hotel in this picture at this beach.

We kept driving south into Kennebunk. We checked out the cute residential houses and downtown area where there was a nice Boulangerie and town ice skating rink.
We kept driving south into Ogunquit, Maine, and drove past the shops and stopped to see the views at Perkins Cove.
After that we stopped at a LLBean Outlet to use the restroom and we simply perused without purchasing anything.
We then rolled back to Boston and prepared for our weeks ahead.
Our trip was short but magical, and it was worth every second. Cheers to being 34 and being in good company!
🌊𓇼🐋🐚 🫐💙